Benzoic acid, 4-(aminomethyl)-, hydrochloride (1:1) → Benzylacetylene

HRID 22872Notes

Reaction equation

HRID 22872 reaction equation
Cl.C([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]N)=[CH:6][CH:5]=1)#N.Cl.[C:13]([C:16]1C=CC(CN)=CC=1)(O)=O.C#CCN1C=CN=N1>>[C:7]1([CH2:8][C:13]#[CH:16])[CH:6]=[CH:5][CH:4]=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 105553Benzoic acid, 4-(aminomethyl)-, hydrochloride (1:1)HCID 99422504-(Aminomethyl)benzonitrile hydrochlorideHCID 127095801-(prop-2-yn-1-yl)-1H-1,2,3-triazole

Product 1

HCID 575753Benzylacetylene

Procedure

Replacing 4-cyanobenzylamine hydrochloride in Example 4, Step (1), with 4-carboxy-benzylamine hydrochloride, and replacing the 1-propyn-3-yl-1H-[1,2,3]triazole in Example 4, Step (2), with 3-phenyl-propyne yielded 4-[[3-3-phenethylethynyl-benzoylamino]-methyl}-benzoic acid; 1H-NMR (DMSO-d6) δ 9.2 (m, 1H), 8.0 (s, 1H), 7.8 (m, 4H), 7.6 (d, 1H) 7.2-7.4 (m, 7H), 4.5 (d, 2H), 3.9 (s, 2H) ppm. Mp 209° C.-211° C.

Sources & evidence

ORD record
ord-e7347b90b4d94e468a7358d3e30b61e9
Source dataset
uspto-grants-2005_02
Patent number
US06849648B2

Reaction notes

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